Structure and Mechanism in Cinchona Alkaloid Chemistry: Overturning a 50-Year-Old Misconception

Angew Chem Int Ed Engl. 1999 Sep;38(17):2539-2543. doi: 10.1002/(sici)1521-3773(19990903)38:17<2539::aid-anie2539>3.0.co;2-c.

Abstract

Long-standing errors of the supposedly established literature, including textbooks and data bases have been corrected: The structure of the hetero-cinchona bases in the crystal and in solution (see scheme) and the mechanism of their formation from quinine and quinidine have been elucidated.